A black detective becomes embroiled in a web of danger while searching for a fortune in missing drug money. During the course of his investigation, he encounters various old connections, ultimately confronting the criminal responsible for Shame’s expulsion from the force. He must also deal with two women, Angela, a beautiful old flame, and Peaches, his energetic but annoying sidekick.

Young urban professionals Jesse (Arye Gross) and his girlfriend Kate (Lar Park Lincoln), move into an old mansion that has been in Jesse’s family for generations. They are soon joined by Jesse’s goofy friend Charlie (Jonathan Stark), who brought along his diva girlfriend Lana (Amy Yasbeck), in the hopes of being discovered by Kate, who works for a record company. Jesse has returned to this old family mansion after his parents were murdered when he was a baby. While going through old things in the basement, Jesse finds a picture of his great-great grandfather (and namesake) in front of a Mayan temple holding a crystal skull with jewels in the eyes. In the background is a man Jesse learns is Slim Razor, a former partner of his great-great grandfather turned bitter enemy after a disagreement over who would get to keep the skull.

Nerdy high schooler Ronald Miller rescues cheerleader Cindy Mancini from parental punishment after she accidentally destroys her mother’s designer clothes. Ronald agrees to pay for the $1,000 outfit on one condition: that she will act as though they’re a couple for an entire month. As the days pass, however, Cindy grows fond of Ronald, making him popular. But when Ronald’s former best friend gets left behind, he realizes that social success isn’t everything.